Toluene → Mepanipyrim

HRID 2166250Notes

Reaction equation

HRID 2166250 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]=[C:16](Cl)[CH3:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(#N)C.C1(C)C=CC=CC=1>O>[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

Product 1

HCID 86296MepanipyrimYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 50 ml reaction flask equipped with a stirrer, a thermometer and a condenser, 5.2 g (0.02 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine, 2.4 g (0.06 mol) of NaOH powder and 50 ml of acetonitrile were charged, and the mixture was reacted at room temperature for 5 hours. After the reaction, toluene and water were added to the reaction mixture, followed by liquid separation. The toluene layer was washed with water. The toluene layer was concentrated and subjected to column chromatography to obtain 1.67 g of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine having a melting point of from 125° to 126° C. The yield was 36%.

Workup

  1. customInto a 50 ml reaction flask
  2. customequipped with a stirrer
  3. customthe mixture was reacted at room temperature for 5 hours
  4. additionwere added to the reaction mixture
  5. customfollowed by liquid separation
  6. washThe toluene layer was washed with water
  7. concentrationThe toluene layer was concentrated

Sources & evidence

ORD record
ord-5b56d45755b44fce96c7a0b4569497f1
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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